Now that Oscar season is upon us, a deluge of commentary is sure to crop up on the Web about the various disappointments: the black actors who weren’t nominated, those who were nominated but weren’t deserving, and the default (legitimate) argument that there just aren’t enough quality roles for black actors.

Editor's note: As 2013 comes to an end, I'll be reposting some of our most popular pieces published during the year. Those who've already read each one can obviously skip them, or revisit if you'd like. For those who joined us later in the year, missing many of these posts from earlier in the year, they will probably be new items. Here's the first of many to come, which I thought was perfectly timed, as we are now deep in awards season, with the 2014 Oscar nominations scheduled to be announced in about 2 weeks from now, and several black actors and directors in the mix. Happy New Year to you all!

Now that Oscar season is upon us, a deluge of commentary is sure to crop up on the Web about the various disappointments: the black actors who weren’t nominated, those who were nominated but weren’t deserving, and the default (legitimate) argument that there just aren’t enough quality roles for black actors.

We at Shadow & Act thought it would be fun to take a few steps back and look at the past 20+ years of black Oscar winners and evaluate whether an Oscar is all that it’s cracked up to be, especially if you’re black in Hollywood. What is it really worth in terms of a black actor’s career? What kind of political minefield must one tap dance on? Does it guarantee more money? Are black actors welcomed into the coveted A-List? And perhaps most important: Will said black Oscar winner be working in the next two, three years? And if so, will it be Oscar-caliber work or the same old stereotypes?

In the last two decades, give or take, we’ve seen the largest number of black Oscar winners. Ten to be exact: five men and five women. Regrettably not equally distributed in categories of leading and supporting roles or along gender lines. As we know black actresses have a harder time winning and getting roles as leading ladies.

Let’s take a close look at the 10 Oscar winners, examining whether the Oscar has made a difference, if at all, to their careers.

Whoopi Goldberg won Best Supporting Actress in 1990 for playing Oda Mae Brown in Ghost making her the second African American woman to win in the category of Best Supporting Actress. Her predecessor is Hattie McDaniel who won for playing Mammy in Gone With the Wind (1939). Few actors—black or white—can hold a candle to Ms. Goldberg. Disappointingly, however, her best work happened in the 1980s culminating with Ghost (1990). Her biggest films Post-Oscar include Sister Act (1992), Sarafina (1992) and Corrina, Corrina (1994). Part of the disappointment is that Hollywood didn’t seem to know what to do with Ms. Goldberg who is both hysterically funny and a dramatic force on screen. In several previous interviews, Ms. Goldberg talked openly about directors giving her a hard time because of her looks. On the whole, Ms. Goldberg’s Oscar seems inconsequential as she hasn’t headlined a major film since Sister Act 2 (1992) and she’s gone into semi-retirement making appearances on television shows and becoming a talking head on the talk show, The View.

Cuba Gooding, Jr won Best Supporting Actor in 1996 for playing Rod Tidwell in Jerry Maguire where his performance is best summarized by the line he made famous: “Show Me The Money.” For the most part, the Oscar win has allowed Gooding to work steadily in a slew of major films alongside phenomenal co-stars. We could argue, however, that his output has been a bit uneven. I’m not sure how you recover from doing a film like Rat Race (2001) though it remains one of my favorites to date. Another bomb of a film is Radio (2003) that I maintain made a poor attempt at being a black version of Forrest Gump. Add to that, Gooding has been seriously typecast as a boy scout. Rarely, if ever, have I seen Gooding play against type, something different and challenging. I expect nothing less from an Oscar winner.

Halle Berry won Best Lead Actress in 2001 for playing Leticia Musgrove in Monster’s Ball amid a sandstorm of controversy. The win made Halle Berry the first black woman to win in the category of Lead Actress. What’s fascinating about Ms. Berry’s career is that she’s repeatedly told reporters that her beauty has been a hurdle in her career. Winning an Oscar definitely catapulted Halle Berry into the upper echelons of Hollywood. Her output post-Oscar has been uneven but lucrative I gather from reports. Her best work happened pre-Oscar: playing in Jungle Fever (1991), Boomerang (1992) and Queen (1993), a television mini-series. What’s interesting to note is that Ms. Berry has used her relative clout in Hollywood to produce some high quality film projects including Introducing Dorothy Dandridge (1999) a TV movie; Lackawanna Blues (2005), also a TV movie; and the obscure stand out film that hardly anyone was able to see Frankie & Alice (2010). Winning an Oscar for Ms. Berry, has been double-edged, you almost get the sense that she (like most black actresses) want to stretch and show off their acting chops but the scripts attached to the big budgets don’t seem to be making their way to her.

That same year, Denzel Washington won his second Oscar for portraying Det. Alonzo Harris in Training Day (2001) for which he won Best Lead Actor. Washington’s first Oscar was for Best Supporting Actor in the film Glory (1989.) The very night that Washington won his Oscar, the Academy also gave a special honor to Sidney Poitier for his illustrious career. At the podium, Washington looks at Poitier and says, “I’ll always be chasing after you, Sidney.” It’s a challenge to gauge whether the second Oscar added much to Washington’s already enviable acting career. In terms of Washington’s output, it seems that his career is evenly split between his two Oscars. In his early career, Washington’s mostly acclaimed and memorable roles were his historic/biographical film roles such as Glory (1989), Cry Freedom (1987) and Malcolm X (1992). His recent work is so radically different from his earlier work that it almost as if another actor has switched places with Mr. Washington. Some might say this is a testament to his A-List status and how much of a brand Denzel Washington has become. It’s been reported widely that he commands around $20 Million per movie. Not many actors can make this claim—black or white. Yet still his recent work, in my view, has been underwhelming.

Jamie Foxx won Best Lead Actor in 2004 for playing Ray Charles in Ray. The multitalented actor—who also sings and tells jokes—has been reaping all of the rewards of an Oscar win as his film projects have been steadily impressive since Ray, lifting him in stature in Hollywood. Mr. Foxx is an incredibly versatile talent, equally comfortable playing serious or funny or supporting and or leading roles. The hoopla surrounding his recent lead role in the controversial Django (2012) suggests that Mr. Foxx will continue to climb. Reports indicate that the Texan-born actor earns approximately $10 Million per movie. It will be interesting to see if Foxx will take on more period films in the vein of Django. It’s definitely a first for the actor, and given its commercial success, people seem to be responding.

Morgan Freeman won Best Supporting Actor in 2004 for playing Eddie Scrap-Iron Dupris in Million Dollar Baby. It’s been said that many actors receive Oscars for their careers, not always for a stand out performance. This is my suspicion with Morgan Freeman’s win in 2004. Almost everyone talks about Freeman’s acclaimed performances in Driving Miss Daisy (1989) and The Shawshank Redemption (1994.) For a career spanning over four decades, this Oscar win didn’t help much in terms of visibility, as he was already a veteran actor when he won in 2004. However, it most likely has helped in terms of larger pay and steadily landing plum roles in major films. How many actors have played God? In terms of quality of roles, I’d be remiss if I didn’t say that a large body of Morgan Freeman’s work occupies the mentor/sidekick stereotype. Granted this could be a consequence of his age but older actors ought to be fully realized as human as well. To date, my personal favorite is his portrayal of Principal Joe Clark in Lean on Me (1989).

Forest Whitaker won Best Lead Actor in 2006 for playing Idi Amin in The Last King of Scotland. Forrest Whitaker is an actor’s actor. Probably the most talented of all the male winners on this list—a male peer of Whoopi Goldberg. In the past six years since snagging the Academy win for his portrayal of Idi Amin, Whitaker has done some television and voice work along with an array of cop flicks including Vantage Point (2008) and Freelancers (2012.) It would be nice to see Whitaker in more dramatic roles as the gun-totting cop role is a bit nondescript. Anyone can do those kinds of movies. But not every actor can transform into a character the way Forrest Whitaker can. His best work has been in supporting roles in small films like The Great Debaters (2007) and the television film The Feast of All Saints (2001.) His work behind the screen are equally stellar; take a look at his producing credits. It’s nice to know that a talent of this caliber isn’t afraid to roll up his sleeves and help bring projects to the light of day.

Jennifer Hudson won Best Supporting Actress in 2006 for playing Effie White in Dreamgirls. The American Idol alumna’s relatively short-lived stardom was multiplied and taken through the roof with the adaptation of Dreamgirls (2006) to the silver screen. Hudson was already a household name during her tenure with American Idol. However winning the Oscar put her on the fast track as an actor. Since winning the Oscar, Hudson has gone on to play in films Sex in the City (2008), The Secret Life of Bees (2008) and Winnie (2011.) With more dramatic roles, Hudson may well “have it all” picking up where Whitney Houston left off.

Mo’Nique won Best Supporting Actress in 2009 for playing Mary in Precious. Outside of her short-lived late night show on BET, we haven’t seen much of Mo’Nique. We all remember the flower that adorned her hair on Oscar night, a nod to the late Hattie McDaniel, who was the first African American actress to win an Oscar in the category of Best Supporting Actress. There have been many reports, including on this site, of Mo’Nique’s interest in playing the late Hattie McDaniel. It’s too soon to say how the Oscar has impacted Mo’Nique’s career that deliberately exists on the fringes of Hollywood.

Octavia Spencer won Best Supporting Actress in 2011 for playing Minny Jackson in The Help. It’s probably too soon to make any predictions on how this Oscar may have helped Octavia Spencer’s career. Spencer is a comedic actress mostly and this was the first time I’ve seen her play a dramatic role. Because so much of the roles for black actors are saturated in stereotypes, Spencer’s role as a complicated and sassy domestic might earn her some extra jobs in Hollywood. Spencer has described her Oscar win as a “needle mover” not overstating its ability to bump her career by any stretch in a recent interview and post on Shadow & Act.

If anything, this exercise has shown that winning an Oscar promises absolutely nothing to actors—black or white. Hollywood is particularly ungenerous to actresses, particularly actresses of color. But I shy away from making too many comparisons to white actors because their path to the Oscars are almost always worlds different from their black colleagues in terms of pay, production budgets, and caliber of scripts.

When asked was the problem with few quality roles for black actors a matter of racism, Oscar-nominated actress Viola Davis responded that many of the scripts that she receives are written by up-and-coming black screenwriters and most of the roles presented to her are of urban crack-addicted mothers. (Here’s the link: skip to 5:10.)

In short, on all levels there needs to be a sharing of responsibility—from deep pockets to young independent filmmakers—to ensure that black actors, especially actresses, are given an opportunity to be recognized for all of the training and tenacity it took to get to Hollywood.

Abdul Ali is a culture writer who lives in the nation’s capital. You can follow him on Twitter.